IP Library Granted Patent US 9,246,104
Granted Patent B2
US 9,246,104 · App. 14/036,189 · Granted Jan 26, 2016

Fullerene derivative, method of manufacturing fullerene derivative and solar cell

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Quick Facts
Patent No.
US 9,246,104
App. No.
14/036,189
Granted
Jan 26, 2016
Kind
B2
Abstract

A fullerene derivative represented by the following formula (1): wherein “FLN” represents a fullerene core, R 1 represents an optionally substituted C 1 -C 24 alkyl group or an optionally substituted C 7 -C 24 aralkyl group, R 2 and R 3 independently represent a hydrogen atom or an optionally substituted C 1 -C 24 hydrocarbon group but excluding a case where both of R 2 and R 3 are hydrogen atoms, and R 2 and R 3 may combine together to form a ring.

Claims (29)

1. A fullerene derivative represented by the following formula (1):

wherein “FLN” represents a fullerene core selected from a group consisting of fullerene C 60 , fullerene C 70 , fullerene C 76 , fullerene C 78 , fullerene C 82 and fullerene C 84 ,

wherein R 1 represents substituted or non-substituted C 1 -C 24 alkyl group or substituted or non-substituted C 7 -C 24 aralkyl group,

the aralkyl group being selected from a group consisting of a benzyl group, a 2-phenylethyl group, a 1-phenylethyl group and a 3-phenylpropyl group,

when the alkyl group or the aralkyl group is substituted, the substituent group being selected from a group consisting of a C 1 -C 10 hydrocarbon group, a C 1 -C 10 alkoxy group, a C 6 -C 12 aryloxy group, a C 1 -C 10 acyloxy group, a C 1 -C 10 oxycarbonyl group, a C 1 -C 10 acyl group, a nitro group, an amino group, an amide group, a nitrile group, a silyl group, a phosphine group and a halogen atom;

wherein R 2 and R 3 independently represent a hydrogen atom or substituted or non-substituted C 1 -C 24 hydrocarbon group but excluding a case where both of R 2 and R 3 are hydrogen atoms, and R 2 and R 3 may combine together to form a ring,

the C 1 -C 24 hydrocarbon group being selected from a group consisting of an alkyl group, an aromatic group, and an aralkyl group,

the aromatic group being selected from a group consisting of a phenyl group, an indenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a fluorenyl group and a pyrenyl group,

the aralkyl group being selected from a group consisting of a benzyl group, a 2-phenylethyl group, a 1-phenylethyl group and a 3-phenylpropyl group,

when the C 1 -C 24 hydrocarbon group is substituted, the substituent group being selected from a group consisting of a C 1 -C 10 hydrocarbon group, a C 1 -C 10 alkoxy group, a C 6 -C 12 aryloxy group, a C 1 -C 10 acyloxy group, an aldehyde group, a C 1 -C 10 oxycarbonyl group, a C 1 -C 10 acyl group, a nitro group, an amino group, an amide group, a nitrile group, a silyl group, a phosphine group and a halogen atom.

2. The fullerene derivative according to claim 1 , wherein the fullerene core represented by “FLN” is at least one of fullerene C60 and fullerene C70.

3. The fullerene derivative according to claim 1 , wherein the fullerene core represented by “FLN” is fullerene C60.

4. The fullerene derivative according to claim 1 , wherein R 1 is a benzyl group without a substituent group, or with at least one substituent group on a corresponding position of the benzene ring selected from a group consisting of a C 1 -C 10 hydrocarbon group, a C 1 -C 10 alkoxy group and a C 1 -C 10 oxycarbonyl group.

5. The fullerene derivative according to claim 1 ,

wherein R 1 is selected from a group consisting of a benzyl group without a substituent group, or with one or more substituent groups on one or more positions of the benzene ring selected from a group consisting of a C 1 -C 10 hydrocarbon group, a C 1 -C 10 alkoxy group and a C 1 -C 10 oxycarbonyl group.

6. The fullerene derivative according to claim 5 ,

wherein the C 1 -C 10 hydrocarbon group is selected from a group consisting of methyl, ethyl, propyl, butyl, phenyl, naphthyl, indenyl, tolyl, xylyl and benzyl,

wherein the C 1 -C 10 alkoxy group is selected from a group consisting of a methoxy group, an ethoxy group, a propoxy group, a butoxy group and a benzyloxy group, and

wherein the C 1 -C 10 oxycarbonyl group is selected from a group consisting of a methoxycarbonyl group and a hexyloxycarbonyl group.

7. The fullerene derivative according to claim 5 ,

wherein R 1 is a benzyl group without a substituent group, or with one or more substituent groups on one or more positions of the benzene ring selected from a group including a methoxy group, and a methoxycarbonyl group.

8. The fullerene derivative according to claim 1 ,

wherein R 1 is selected from a group consisting of 2-OMe-C 6 H 4 —CH 2 —, 3-OMe-C 6 H 4 —CH 2 —, 4-MeOC 6 H 4 —CH 2 —, 4-CH 3 (CH 2 ) 5 O 2 C—C 6 H 4 —CH 2 —, 2-MeO-4-CO 2 MeC 6 H 3 —CH 2 — and BnOCH 2 CH 2 CH 2 —, where Me represents CH 3 — and Bn represents a benzene ring.

9. The fullerene derivative according to claim 1 ,

wherein R 2 R 3 N— is selected from a group consisting of a methylamino group, an ethylamino group, a n-propylamino group, an isopropylamino group, a n-butylamino group, an isobutylamino group, a n-hexylamino group, a benzylamino group, a phenylamino group, a tolylamino group, a dimethylamino group, a diethylamino group, a di(n-propyl)amino group, a diisopropylamino group, a di(n-butyl)amino group, a diisobutylamino group, a di(n-hexyl)amino group, a dibenzylamino group, a diphenylamino group, a ditolylamino group, a methylphenylamino group, a piperidino group, a morpholino group, a thiomorpholino group and a tetrahydroisoquinolino group.

10. The fullerene derivative according to claim 1 ,

wherein R 2 R 3 N— is a morpholino group.

11. The fullerene derivative according to claim 1 ,

wherein R 2 R 3 N— is selected from a group consisting of a dibenzylamino group, a benzylamino group, an N-methylaniline group, a diethylamino group, a dibutylamino group, a tetrahydroisoquinoline group, a thiomorpholino group, a morpholino group, a piperidyl group and an 1-phenylpiperazine group.

Assignments (4)
CHANGE OF ADDRESS Recorded Feb 14, 2024
From: RESONAC CORPORATION
To: RESONAC CORPORATION
Reel/Frame 066599/0037 →
CHANGE OF NAME Recorded Jun 23, 2023
From: SHOWA DENKO K.K.
To: RESONAC CORPORATION
Reel/Frame 064082/0513 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 19, 2017
From: SHOWA DENKO K.K.
To: SHOWA DENKO K.K.; MITSUBISHI CORPORATION
Reel/Frame 041016/0731 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 25, 2013
From: JIN, TIENAN; SI, WEILI; YAMAMOTO, YOSHINORI; IGARASHI, TAKESHI
To: SHOWA DENKO K.K.; TOHOKU UNIVERSITY
Reel/Frame 031276/0338 →